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Dimethylformamide → HCID 91588840, compound

HRID 2307757
Notes
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Reaction equation

HRID 2307757 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([O:9][CH2:10][C@@H:11]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH:6]=[N:7][CH:8]=1)#[CH:2].Cl.Br[C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1.CN(C=O)C.C(N(CC)CC)C>[Cu]I.C(OCC)(=O)C>[NH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([CH2:12][C@H:11]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:28])[CH3:27])[CH2:10][O:9][C:5]2[CH:6]=[N:7][CH:8]=[C:3]([C:1]#[C:2][C:32]3[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=3)[CH:4]=2)=[CH:14]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 881004-Bromopyridinium chlorideHCID 91060211HCID 91060211, compound

Product 1

HCID 91588840HCID 91588840, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of Example 14B (150 mg, 0.384 mmol), 4-bromopyridine hydrochloride (75 mg, 0.34 mmol), Pd2Cl2(PPh3)2 (27 mg, 0.0384 mmol), and CuI (18 mg, 0.093 mmol), was purged with nitrogen, treated with DMF (4 mL) and triethylamine (214 μL, 1.54 mmol), stirred at 50° C. for 20 hours, cooled to room temperature, treated with ethyl acetate (50 mL), washed with brine, dried (MgSO4), filtered, and concentrated. The residual oil was purified by flash column chromatography on silica gel with 2:1 ethyl acetate/hexanes to provide the desired product (122 mg, 68%). MS (APCI) m/e 469 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residual oil was purified by flash column chromatography on silica gel with 2:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-78292f70298b4febad8201fb18182849
Source dataset
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06831175B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes